Methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate → Methyl 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoate

HRID 422558Notes

Reaction equation

HRID 422558 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([C:22](=[CH2:27])[C:23]([F:26])([F:25])[F:24])=[N:17][N:16]=[CH:15]2>CO.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH:22]([CH3:27])[C:23]([F:26])([F:24])[F:25])=[N:17][N:16]=[CH:15]2

Participants

4

Reactant 1

HCID 66675460Methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate

Product 1

HCID 66675245Methyl 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoateYield 45.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate (200 mg, 537 μmol) in methanol (3000 μl) was added palladium (10 wt. % on activated carbon; 22.9 mg, 215 μmol) and hydrogenated (double-walled balloon pressure) at room temperature for 20 h, during which LC-MS indicated complete conversion. The reaction was filtered via a pad of Celite®, and the filtrate was concentrated in vacuo and purified by CombiFlash (20% to 80% EtOAc/Hexanes) to afford methyl 4-methyl-3-(1-(1,1,1-trifluoropropan-2-yl)phthalazin-6-yl)benzoate (91.1 mg, 45.3% yield) as a golden yellow foam. MS (ES+): 375.2 (M+H)+.

Workup

  1. filtrationThe reaction was filtered via a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by CombiFlash (20% to 80% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-23d136548c8241758d3901ecd66482c2
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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